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Angew Chem Int Ed Engl. 2015 Jun 8;54(24):7144-8. doi: 10.1002/anie.201501575. Epub 2015 May 4.

Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.

Author information

1
Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368 (USA). keith.fandrick@boehringer-ingelheim.com.
2
Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368 (USA).
3
Research and Development, Boehringer Ingelheim (Canada) Ltd. 2100 Cunard Street, Laval, Québec H7S 2G5 (Canada).

Abstract

A practical and efficient synthesis of a complex chiral atropisomeric HIV integrase inhibitor has been accomplished. The combination of a copper-catalyzed acylation along with the implementation of the BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical. Furthermore, the overall synthesis was conducted in an asymmetric and diastereoselective fashion with respect to the imbedded atropisomer.

KEYWORDS:

Suzuki couplings; acylation; asymmetric synthesis; phosphine ligands; tert-butylation

PMID:
25939331
DOI:
10.1002/anie.201501575
[Indexed for MEDLINE]

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